The Merchant of Venice at the Broadhurst theatre in New York, late 2010-early 2011, starring Al Pacino as Shylock (centre)
Photograph: Joan Marcus/AP

The figure of the unassimilated Jew, defiantly “other” in skullcap, gabardine and fringed garment, has been a source of Gentile unease for centuries. It is what fuels the main plot of The Merchant of Venice, and its corollary – Jew-baiting – is what gives the play its uncomfortable immediacy. We know this story; its ramifications are still playing out: the Holocaust, Israel, Gaza. Part of its disquieting power, in Shakespeare’s telling, is its unstable moral perspective: are we watching a play about antisemitism, or an antisemitic play? Unlike Malvolio, whose expulsion from the festive world of Twelfth Night is a cause for straightforward rejoicing, Shylock’s fall leaves us jangling with unresolved emotion. Yes, he was going to cut his pound of flesh out of Antonio, but he had been provoked: spat upon, robbed of daughter and ducats, goaded beyond endurance. Although Portia gives him every chance to be merciful, there is something faintly shabby about the “no jot of blood” trick she pulls when he refuses (all it really shows is that he has been playing in a rigged game from the start), and there is something downright chilling about the sentence of forced conversion that follows. The last act tinkles on in Belmont without him, as if Shakespeare half wants us to forget this troubling figure before we leave the theatre, but it is the Belmont lovers we forget. Shylock lingers.

Howard Jacobson’s new novel, part of a series of Shakespeare retellings commissioned for the 400th anniversary of the bard’s death, makes bold use of this haunting persistence. In its opening scene, Simon Strulovitch – “a rich, furious, easily hurt philanthropist with on-again off-again enthusiasms, a distinguished collection of 20th-century Anglo-Jewish art … and a daughter going off the rails” – encounters Shylock in a Cheshire graveyard, transported to 21st-century England, but otherwise much as Shakespeare left him. Among Strulovitch’s fitful enthusiasms is the question of what it means to be a Jew – the Finkler question, essentially – and Shylock, who has had plenty of time to reflect on the matter (and who also knows a thing or two about errant daughters), provides him with a natural interlocutor. Locked in the limbo of his own circling rage and regret, Shylock functions as a phantasmal projection of Strulovitch’s conscience, but he is also very much a freestanding character (Jacobson’s relaxed, garrulous style allows both), interacting with other people, and after Strulovitch invites him back to his house, the two men strike up a friendship.

Meanwhile in the Christian world, as per the original, a complicated romcom intrigue assembles itself, with a gay aesthete named D’Anton taking the Antonio role, a Porsche-driving heiress with a reality TV show that combines cooking and counselling playing Portia, a brainless football player with a thing for Jewish girls standing in for Gratiano, and so on. No one in this prosperous corner of Cheshire’s “golden triangle” needs to borrow money from Strulovitch, but dangerous bonds link Gentile and Jew nevertheless. D’Anton has offended Strulovitch in the past by blocking his attempt to create a museum of Anglo-Jewish art; Gratan the footballer has been creeping around Strulovitch’s sexually precocious young daughter; and, in short, Strulovitch has been given ample provocation for exacting his own version of the pound of flesh when the opportunity presents itself to do so.

The Strulovitch/Shylock material, which consists mostly of talking and thinking, is where the novel excels. Jacobson knows these worldly, embattled Strulovitch types with their lurching atavisms and exasperations, inside out. He has done them before, but the tumult remains raw and seething, and Shylock’s presence as accelerant gives it all a freshly tragicomic intensity. A self-mocking humour prevails as Strulovitch wrestles with the “inflamed Jewishness” boiling up inside him under Shylock’s influence: his horror of having his daughter marry a non-Jew; a sudden interest in the principles of kosher; irrepressible urges to denounce the Guardian for driving Jews “to the brink of extermination”; fantastical schemes of vengeance against his enemies … There are passages in these chapters that have a wit and punch reminiscent of Roth at his best, rendering the mutually defining paranoias of Jews and Gentiles with merciless clarity.

Villain or victim, Shakespeare’s Shylock is a character to celebrate

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I wish the same could be said for the “Christian” material. To give credit where it is due, there is something at least theoretically ingenious in the way Jacobson re-engineers the love plots from the original so as to bring about his own large surprises. But the actual execution is crude in the extreme. Flimsily conceived embodiments of vacuousness or effete viciousness, the Christians are also almost all unabashed antisemites. D’Anton and Plury (the Portia character) amuse themselves playing “Jewepithets” (“moneybags”, “pig refuser”); Gratan has been in trouble for giving a Dieudonné quenelle (Nazi salute) on the football field. Some of these qualities, of course, have their warrant in Shakespeare, but there they form part of a coherent set of interests and motivations drawn from an observed cultural reality, whereas here we are in a realm of pure propaganda. Antisemitism is undoubtedly on the rise, but painting your entire Gentile cast as little Julius Streichers only plays into the nastiest antisemitic trope of all: that it is all just a Jewish persecution fantasy. The crassness seems intentional, but I am not sure what the aim is. If humour, it misses (or did for me). Even as payback – a sort of retaliatory blood libel, perhaps – it never gives its targets enough substance to make them worth caring about. Think of, well, think of what Shakespeare did with Shylock.

And yet the novel remains compelling, and if you can ignore the thinness of these sections, there is actually an intriguing thesis being developed. In an earlier incarnation as an academic, Jacobson co-wrote a wonderful book on Shakespeare with the late Wilbur Sanders, Shakespeare’s Magnanimity, and perhaps the most enjoyable thing about Shylock Is My Name is, fittingly, the astute way in which it reads and rereads the play it was commissioned to retell. It does this explicitly, with Strulovich, for example, pressing Shylock to tell him exactly what was going on in his head when he came up with his ill-omened forfeit. But it also does so at a structural level, building on ideas latently present in The Merchant of Venice to bring Shylock’s own story to a surprising but strangely satisfying resolution. There are two big twists at the end. One, involving foreskins, is a bit silly. But the other, in which one of Shakespeare’s great speeches is reallocated to (and reconceived by) the last character on Earth you’d imagine giving it, is inspired. It does what any good literary subversion should do: deepens and enhances one’s appreciation of the original.